α-氟代半乳糖的合成  

Synthesis of α-Galactopyranosyl Fluoride

作　　者：赵晗[1] 刘军[1] 卢丽丽[1] 肖敏[1] 

机构地区：[1]山东大学国家糖工程技术研究中心,山东济南250100

出　　处：《精细化工》2008年第7期660-663,共4页Fine Chemicals

基　　金：国家自然科学基金资助项目(30770065)~~

摘　　要：α-氟代半乳糖是一类重要的1-氟代糖,可在化学-酶法催化过程中作为糖基供体合成各类重要的半乳糖苷化合物,但这类氟代糖的大量获得至今没有完整实用的合成方法。作者以D-半乳糖为原料,将其全乙酰化获得五乙酰基-β-半乳糖,用吡啶-氟化氢络合物在-20℃进行氟化反应,得到四乙酰基-α-氟代半乳糖,然后用甲醇钠/甲醇溶液进行脱乙酰反应,TLC及核磁共振氢谱验证所得产物,成功获得α-氟代半乳糖(δ=5.57,J1,2=2.7,J1,F=53.9 Hz)。α-Galactosyl fluoride is among the most important 1-glycosyl fluorides and can be used as glycosyl donor in the chemo-enzymatic synthesis of galactose containing chemicals. However,there is no integrated method for synthesis of α-galactopyranosyl fluoride so far. In this article,α-galactopyranosyl fluoride was prepared through a series of chemical reactions, including acetylation, fluorination and deacetylation. With D-galactose as the starting material, penta-O-acetyl-β-galactopyranose was obtained,followed by fluorination at -20℃. And then the tetra-O-acetyl-α-galactopyranosyl fluoride was deacetylated in sodium methoxide/methanol. The final product was detected by TLC and identified by NMR （δ =5.57 ,J1.2 =2.7 ,JI.F =53.9 Hz）.

关 键 词：D-半乳糖 1-氟代糖 α-氟代半乳糖 糖基供体 

分 类 号：TQ031.2[化学工程] TQ124.3